2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → N-{3-(cis-3,5-Dimethyl-1-piperazinyl)-4-[(trifluoromethyl)oxy]phenyl}-4-(2-thienyl)benzenesulfonamide

HRID 130463노트

반응식

HRID 130463 반응식
Br[C:2]1[CH:3]=[C:4]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].[CH3:28][C@H:29]1[CH2:34][NH:33][CH2:32][C@@H:31]([CH3:35])[NH:30]1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:28][C@H:29]1[NH:30][C@@H:31]([CH3:35])[CH2:32][N:33]([C:2]2[CH:3]=[C:4]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:5]=[CH:6][C:7]=2[O:8][C:9]([F:12])([F:11])[F:10])[CH2:34]1

참가 물질

7

반응물 4

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 23676156Sodium t-butoxideHCID 69198455N-{3-Bromo-4-[(trifluoromethyl)oxy]phenyl}-4-(2-thienyl)benzenesulfonamide

생성물 1

HCID 59007044N-{3-(cis-3,5-Dimethyl-1-piperazinyl)-4-[(trifluoromethyl)oxy]phenyl}-4-(2-thienyl)benzenesulfonamide

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

The product of Step 2 (162 mg, 0.34 mmol), cis-2,6-dimethyl piperazine (78 mg, 0.68 mmol), sodium tert-butoxide (169 mg, 0.68 mmol), tris(dibenzylideneacetone)dipalladium(0) (16 mg, 0.017 mmol) and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (20 mg, 0.051 mmol) in dioxane (4 ml) were heated in a microwave reactor at 125° C. for 30 minutes. The reaction mixture was applied to an SCX ion exchange cartridge (Varian bond-elute) and washed with methanol and 2M ammonia in methanol. The combined basic fractions were concentrated in vacuo and the residue purified by mass directed autoprep HPLC to afford the title compound (E245). MS (ES+) m/e 512 [M+H]+.

후처리

  1. washThe reaction mixture was applied to an SCX ion exchange cartridge (Varian bond-elute)
  2. washwashed with methanol and 2M ammonia in methanol
  3. concentrationThe combined basic fractions were concentrated in vacuo
  4. customthe residue purified by mass

출처 및 근거

ORD 기록
ord-6c0eb222b8b44af7b6c2cde901ab3206
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381728B2

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